Water → HCID 66942140, compound

HRID 1519194Notes

Reaction equation

HRID 1519194 reaction equation
C([O:3][C:4]([C:6]1[C:11]2[CH2:12][C@@H:13]3[C:18]([CH3:20])([CH3:19])[C@:17]([CH3:21])([C:10]=2[CH:9]=[CH:8][CH:7]=1)[CH2:16][CH2:15][N:14]3[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].O>O1CCCC1>[CH2:22]([N:14]1[CH2:15][CH2:16][C@:17]2([CH3:21])[C:18]([CH3:20])([CH3:19])[C@H:13]1[CH2:12][C:11]1[C:6]([CH2:4][OH:3])=[CH:7][CH:8]=[CH:9][C:10]=12)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 58123592HCID 58123592, compound

Product 1

HCID 66942140HCID 66942140, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (2R,6S)-3-benzyl-6,11,11-trimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocine-10-carboxylic acid ethyl ester (0.96 g) in tetrahydrofuran (2 mL) is added dropwise to LiAlH4 (1.6 mL, 2.4 mol/L in tetrahydrofuran) in tetrahydrofuran (1.5 mL). The reaction mixture is stirred at ambient temperature for 90 min. Then, water (4 mL) is added carefully and the resulting mixture is extracted with ethyl acetate. The combined organic extracts are washed with water and brine and dried (MgSO4). The solvent is removed under reduced pressure to give the product.

Workup

  1. extractionthe resulting mixture is extracted with ethyl acetate
  2. washThe combined organic extracts are washed with water and brine
  3. dry with materialdried (MgSO4)
  4. customThe solvent is removed under reduced pressure
  5. customto give the product

Sources & evidence

ORD record
ord-be000aa25e68480eb2fdab4d3562b2b1
Source dataset
uspto-grants-2015_07
Patent number
US09073870B2

Reaction notes

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